91818-96-1

Upstream product

• 104-63-2 N-Benzylethanolamine 
• 5908-62-3 isothiazolidine 1,1-dioxide 
• 108-88-3 toluene 
• 98572-04-4 (3-Allylsulfanyl-propyl)-benzyl-amine; hydrobromide 
• 98572-08-8 Benzyl-[3-(prop-2-ene-1-sulfinyl)-propyl]-amine 
• 100-46-9 benzylamine 
• 90945-14-5 N-benzyl-3-chloropropane-1-sulfonamide 
• 98572-12-4 N-benzylisothiazolidine 
• 138528-52-6 2-ethyl methanesulfonate 

Downstream Products

• 905975-31-7 (2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-5-yl)-phosphonic acid diethyl ester 
• 905975-47-5 (S)-1-Benzyl-2-[2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-(5Z)-ylidene]-ethylamine 
• 905975-43-1 (S)-1-Benzyl-2-[2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-(5E)-ylidene]-ethylamine 
• 905975-39-5 [1-benzyl-2-(2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl ester 
• 905975-35-1 [1-benzyl-2-(2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl ester 
• 905975-57-7 (S)-2-Amino-4-methyl-pentanoic acid {(S)-1-benzyl-2-[2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-(5E)-ylidene]-ethyl}-amide 
• 905975-52-2 ((S)-1-{(S)-1-Benzyl-2-[2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-(5Z)-ylidene]-ethylcarbamoyl}-3-methyl-butyl)-carbamic acid tert-butyl ester 
• 905975-51-1 ((S)-1-{(S)-1-Benzyl-2-[2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-(5E)-ylidene]-ethylcarbamoyl}-3-methyl-butyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

A new synthesis of sultams from amino alcohols

The base-mediated cyclization of N,O-dimesylate derivatives of cyclic and acyclic amino alcohols provides a simple access to five- and six-member sultams: isothiazolidine-1,1-dioxides and thiazinane-1,1-dioxides respectively.

Copper-catalyzed amination of primary benzylic C?H bonds with primary and secondary sulfonamides

A room-temperature, copper-catalyzed amination of primary benzylic C?H bonds with primary and secondary sulfonamides is described. The reaction is applicable to the coupling of a range of primary and secondary benzylic hydrocarbons with a diverse set of sulfonamides and is tolerant of substitution on both coupling partners. Factors which influence the selectivity of C?H functionalization between primary and secondary sites are examined.

Dipeptide vinyl sultams: Synthesis via the Wittig-Horner reaction and activity against papain, falcipain-2 and Plasmodium falciparum

The synthesis of phosphonate derivatives of N-phenyl- and N-benzyl-γ- and δ-sultams, and their application in the Wittig-Horner reaction with N-Boc-l-phenylalanine aldehyde to afford E- and Z-isomers, are described. These compounds were further processed to provide five dipeptide vinyl sultams, which were found to be inactive against papain at concentrations up to 50 μM. In contrast, vinyl sultams demonstrated weak activity against recombinant falcipain-2 and Plasmodium falciparum W2.

Synthesis of substituted 1,3-propanesultams from N-substituted 2-amino alcohols

Substituted 1,3-propanesultams (isothiazolidine 1,1-dioxides) 3a-c have been prepared via butyllithium-mediated cyclization of the N,O-dimesylates 2a-c of N-substituted 2-amino alcohols 1 a-c.

SYNTHESIS OF N-ALKYLISOTHIAZOLIDINES

N-Alkylisothiazolidines were prepared by -sigmatropic rearrangement of allyl 3-alkylaminopropyl sulfoxides to the sulfenates, followed by intramolecular thiophilic substitution of N-alkylamino moieties.